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Yacht sailing holidays & skippered tours in Tuscany

Discover the magic of sailing holidays in Tuscany! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

74

experiences

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4.7

Seductive weekend on a sailing boat on the island of Elba

Duration:

3 days - 2 nights

Italy:

Tuscany

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+50 travellers

have booked

Starting from

€239

€265

Per person

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Magical weekend on Giglio Island

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€252

€280

Per person

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4.8

Lots of sea and lots of sailing - from Corsica to Tuscany

Duration:

7 days - 6 nights

Italy:

Tuscany

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fabrizia b.

has booked

€562

€624

Per person

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4.7

An itinerant journey: Elba, Pianosa, Giglio, Giannutri, Argentario

Duration:

6 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€711

€790

Per person

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4.7

An itinerant journey: Elba, Capraia and Corsica

Duration:

6 days - 6 nights

Italy:

Tuscany

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+24 travellers

have booked

Starting from

€711

€790

Per person

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4.8

Super!

Cruise in the Gulf of Baratti

Duration:

2 days - 2 nights

Italy:

Tuscany

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+4 travellers

have booked

€189

€210

Per person

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4.8

Barefoot holiday: Weekend between Elba and Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€300

€330

Per person

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4.8

Super!

On board a classic sailing ship between Elba-Capraia-Corsica

Duration:

6 days - 7 nights

Italy:

Tuscany

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+15 travellers

have booked

€475

€500

Per person

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4.7

Discovering the Island of Elba

Duration:

5 days - 4 nights

Italy:

Tuscany

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+2 travellers

have booked

Starting from

€713

€750

Per person

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5.0

Fine Agosto tra Elba , Capraia e Corsica solo per 4 ospiti

Duration:

5 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€831

€875

Per person

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5.0

Cruise between Elba, Corsica Del Nord and Capraia with PROFESSIONAL SKIPPER AND COOK

Duration:

6 days - 7 nights

Italy:

Tuscany

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+77 travellers

have booked

Starting from

€713

€750

Per person

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4.9

Super!

Long weekend on the Island of Elba with friends

Duration:

4 days - 3 nights

Italy:

Tuscany

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+40 travellers

have booked

Starting from

€266

€280

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Tuscany

3129 reviews

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Holiday and sailing school between the Tuscan archipelago and Corsica

07/26/2024

RITA M.

-

Italy

Bellissima esperienza, consiglio vivamente anche a chi come ma è alle prime armi in questa attività che ti riconnette alla natura e al tuo io interiore, Un grazie particolare a Diego skipper competente, paziente e alla mano, specialie il suo sugo tonno e origano assolutamente da provare.Ottima la compagnia! 💚
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A dream adventure in the Tuscan Archipelago

07/26/2024

Pietro D.

-

Italy

È stata una bellissima esperienza, Ho potuto godere del mare,e dell' avventura grazie alla barca Dali. L' esperienza e la pazienza del comandante Livio ci ha permesso di partecipare alle manovre di bordo. La compagnia è stata fantastica, la tranquillità, e la serenità hanno regnato. Buon vento!
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5 days sailing the Tuscan Archipelago

07/25/2024

Elisa M.

-

Italy

Condividiamo i commenti di Sara e Giulia, aggiungendo che Antony ha anche preparato degli ottimi pasti. Le cabine sono comode e confortevoli. Abbiamo goduto pienamente il mare, la navigazione, la compagnia. Spese extra contenute come promesso.
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Elba, Corsica and Capraia sailing

07/23/2024

Sonia P.

-

Belgium

Ottima esperienza! Luoghi incantevoli, bagni in acque cristalline, impeccabile organizzazione dell’itinerario di viaggio e della vita a bordo da parte dello skipper Marino, che conosce bene i luoghi e si prodiga per offrire alla ciurma una vacanza indimenticabile.

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Tuscany: the best travel ideas

Other travel ideas

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